Probably people just need two email clients: One for non-secure email, another that only sends secure messages. They can both use imap for the same account. Bonus: spam might potentially have a hard time getting accepted as a secure sender, leaving secure email spam free. Alternately, do it on viewing / editing via plugins that are less invasive and more secure. There are several problems: Choosing an ID system: email address + key ID of some kind. Key exchange / trust system: Hierarchical (do you trust some or all CAs? Their signup policies?), web of trust (GPG or similar), personal signing, etc. Visibility and understanding: Current systems are annoying even for experts. No hope of a normal user looking at or understanding ID/cert/key trust situation. Make it specific and simple: CA is safe but could be coopted by TLA or mistakes, signup was weak (could have been a stolen credit card), password could have been stolen, mitm exposure, etc. Just draw the trust / exploit tree. Factor in multi-factor, alternate channel checking, etc. Ease of selecting, enabling, and using read/write interfaces. Solve the problems of control, time available, ability to save for later safely. Stephen On 4/20/14, 10:55 PM, Scott Blaydes wrote:

On Apr 20, 2014, at 7:05 PM, coderman wrote:

...

we have the maths! we have the technology!

... yet actual robust, private communications remain elusive.

where the "Great Filter" thwarting our privacy codes?

is it usability; anything more than invisibly automatic a failure? Yes. People keep claiming that it is just too hard to encrypt email. There are plugins for all platforms. If you can’t send encrypted email, sending email in the first place is probably too difficult, just txt everyone on your fone. The smartfone has made for such stupid people that if it can’t be done in just a few keystrokes (content included) then it is too hard or tl;dr.

Remember the old days when there wasn’t PPP and SLIP connections? Before broadband. When a conversation on IRC was enjoyable, the right amounts of humor and actual thought? And you knew not to ask for help in #unix on efnet.

...

is it cost; anything more than zero too much to bear in the market?

No, everyone can afford a smartfone now a days.

...

is it correctness; anything less than a single mode always secure, broken? Life is full of levels of grey, and so is security. That password you use on new sites you don’t trust vs your gpg/pgp passphrase. The sheeple don’t have levels of grey with regards to security, either take it to their grave or everyone can see.

Chatting with someone who was looking to start his own desktop Linux distro. I suggested an encrypted messaging platform over the security-hole-riddled platform he was using and he told me he had nothing to hide. I told him he wasn’t the kind of person who should be developing anything security related.

Security takes effort that people are not will to expend.

...

perhaps all of these above, each a requisite element of robustness, further compounding the difficulty of realizing an ideal.

-- Stephen D. Williams sdw@lig.net stephendwilliams@gmail.com LinkedIn: http://sdw.st/in V:650-450-UNIX (8649) V:866.SDW.UNIX V:703.371.9362 F:703.995.0407 AIM:sdw Skype:StephenDWilliams Yahoo:sdwlignet Resume: http://sdw.st/gres Personal: http://sdw.st facebook.com/sdwlig twitter.com/scienteer

On May 5, 2014, at 9:05 AM, rysiek wrote:

Dnia poniedziałek, 21 kwietnia 2014 00:30:42 Stephen D. Williams pisze:

...

Probably people just need two email clients: One for non-secure email, another that only sends secure messages.

Well, instead of the latter, one can use RetroShare with great results: http://retroshare.sourceforge.net/

You can use it as a replacement for other kinds of communication, too. Like VoIP: http://rys.io/en/129

-- Pozdr rysiek

You had me till this line in the description: "using a web-of-trust to authenticate peers and OpenSSL to encrypt all communication” Not feeling like trusting more things to OpenSSL right now. Lets see how LibreSSL turns out and see if it can be switched. Scott

On Fri, 09 May 2014 13:36:54 +0200 rysiek wrote:

Dnia wtorek, 6 maja 2014 20:27:04 Scott Blaydes pisze:

...

On May 5, 2014, at 9:05 AM, rysiek wrote:

...

Dnia poniedziałek, 21 kwietnia 2014 00:30:42 Stephen D. Williams pisze:

...

Probably people just need two email clients: One for non-secure email, another that only sends secure messages.

Well, instead of the latter, one can use RetroShare with great results: http://retroshare.sourceforge.net/

You can use it as a replacement for other kinds of communication, too. Like VoIP: http://rys.io/en/129

You had me till this line in the description: "using a web-of-trust to authenticate peers and OpenSSL to encrypt all communication” Not feeling like trusting more things to OpenSSL right now. Lets see how LibreSSL turns out and see if it can be switched.

Good point; still better than most alternatives. One biggie for me is that there is no way to send an unencrypted message via RetroShare. I.e. no way for the user to fsck up.

I find OpenSSL use in RetroShare a smaller problem than the fact that a user of any GPG-enabled e-mail client can actually send an unencrypted e-mail and... not notice that until its too late. Not to mention metadata (sender, addressee, topic, etc, not being GPG-encrypted).

SSL is broken and the metadata is in fact a huge problem. Also, users want the convenience of a webinterface or to keep their existing email clients. In my opinion, that problems can only be solved by a hardware solution. We just did that. Here is how it works: https://enigmabox.net/en/cjdns-en/ Cheers, 42 -- 42 <42@enigmabox.net>

Interesting. Is there software I can run on my own machine? I am not a "regular joe", I want some more control even if it means a bit less convenience. Understandable. Currently, we use Debian, but moving to OpenWRT, which is in test phase at the moment. When we're done, I'll offer dd images for flashing your own CFcard. Until then, you may build your own image

directly: https://github.com/enigmagroup/enigmabox-openwrt Its tailored for the PC-Engines alix2d3 board. If you have such boards, you can set up a network of Enigmaboxes at home; or join the Projectmeshnet IRC channel and ask for a peering - or set up your own servers. And no, there is no "software" that you can run on your machine for that. You *want* to run it on an embedded device, so that you can power off your workstation and still be able to receive emails or phone calls. Best regards, 42 -- 42 <42@enigmabox.net>

On Sat, 24 May 2014 15:56:33 +0200 rysiek wrote:

...

And no, there is no "software" that you can run on your machine for that. You *want* to run it on an embedded device, so that you can power off your workstation and still be able to receive emails or phone calls.

Well, that's for me to decide, isn't it. :) I understand the rationale for this, but might I suggest choosing a different way of putting it in words? The power of FOSS is the unimaginable -- things people do with our software that we never even thought of. Yes, of course. Sorry, I didn't want to overrun your freedom of decision. And I'm curious by myself where it may take us... :)

Apart from that it looks really good. Thanks! Thank you too! Great to hear.

-- 42 <42@enigmabox.net>